Isopropenyl acetate → HCID 3023180, compound

HRID 542631Notes

Reaction equation

HRID 542631 reaction equation
[C:1]1(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10](OC(C)=C)(=[O:12])[CH3:11]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[C:10]([O:9][C:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 7916Isopropenyl acetateHCID 10403Cyclooctanone

Product 1

HCID 3023180HCID 3023180, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 10340Sodium CarbonateCatalyst

Procedure

In the presence of 0.6 g of para-toluenesulfonic acid, 50 g (0.4 mol) of cyclooctanone and 100 ml (0.9 mol) of isopropenyl acetate were refluxed for 11 hours. The reaction mixture was cooled, stirred with 0.6 g of anhydrous sodium carbonate at room temperature for one hour, left standing overnight, and filtered. The filtrate was distilled under reduced pressure to afford 60 g (91% in yield) of 1-cyclooctenyl acetate having a boiling point of 71° to 73° C./3 mmHg.

Workup

  1. temperatureThe reaction mixture was cooled
  2. waitleft
  3. filtrationfiltered
  4. distillationThe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-bd229259e0f845dbae6339c145bc1257
Source dataset
uspto-grants-1987_04
Patent number
US04658055

Reaction notes

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